2-取代酰氨基-5-(α-龙脑烯醛基)-1,3,4-噻二唑化合物的合成及抑菌活性
Synthesis and Antifungal Activities of 2-Sustituted Acylamino-5-(α-campholenic aldehyde)-based-1, 3, 4-thiadiazole Compounds
-
摘要: 以α-蒎烯为原料,先经环氧化和催化异构得到α-龙脑烯醛,再与氨基硫脲反应得到α-龙脑烯醛基缩氨基硫脲,然后环合生成α-龙脑烯醛基噻二唑,最后将其与一系列酰氯发生N-酰化反应,合成得到12个未见文献报道的2-取代酰氨基-5-(α-龙脑烯醛基)-1,3,4-噻二唑化合物(6a~6l)。通过FT-IR、1H NMR、13C NMR和ESI-MS对12个目标产物进行结构表征,并对目标产物的抑菌活性进行了测试。抑菌活性测试表明:在50 mg/L质量浓度下,目标化合物对5种供试病菌均有不同程度的抑制活性,部分目标化合物的抑菌活性与商品抑菌剂嘧菌酯相近,甚至超过嘧菌酯,其中目标化合物6j对小麦赤霉病菌(Fusarium graminearum)的抑菌率达94.4%, 6h对苹果轮纹病菌(Physalospora piricola)的抑菌率达97.7%。Abstract: α-Campholenic aldehyde was prepared by the epoxidation and catalytic isomerization of α-pinene.Then, α-campholenic aldehyde-based thiadiazole was prepared by the cyclization reaction of α-campholenic aldehyde-based thiosemicarbazone, which was obtained by the reaction of thiosemicarbazide with α-campholenic aldehyde.Finally, twelve novel 2-sustituted acylamino-5-(α-campholenic aldehyde)-based-1, 3, 4-thiadiazole compounds (6a-6l) were synthesized by the N-acylation reactions of α-campholenic aldehyde-based thiadiazole with a series of acyl chlorides.The target compounds were characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS.Antifungal activity test showed that, at the concentration of 50 mg/L, the target compounds exhibited different antifungal activities against the five tested fungi.Some of them exhibited antifungal activities were close to or even better than the commercial azoxystrobin used as positive control in this study.Among them, in which compound 6j had an inhibition rate of 94.4% against Fusarium graminearum, and compound 6h had an inhibition rate of 97.7% against Physalospora piricola.